This guy seems like a poster child of what's wrong with sports writing today. You have all these objectively lousy writers trying to shoehorn ruthlessly unfunny jokes into every other sentence and using questions as literary devices.
It all stems from Bill Simmons, who combined being unfunny (he, at least, has a semblance of a sense of humor) with being a savvy self-promoter and Internet marketer and turned himself into the most popular active sports writer. And now a whole generation of sportswriters who will work for peanuts are trying their best to emulate him. It's awful.